WO2019132374A1 - 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치 - Google Patents

유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치 Download PDF

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WO2019132374A1
WO2019132374A1 PCT/KR2018/016133 KR2018016133W WO2019132374A1 WO 2019132374 A1 WO2019132374 A1 WO 2019132374A1 KR 2018016133 W KR2018016133 W KR 2018016133W WO 2019132374 A1 WO2019132374 A1 WO 2019132374A1
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group
substituted
unsubstituted
compound
formula
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French (fr)
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이한일
김병구
박영성
신창주
유동규
이승재
장기포
정성현
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삼성에스디아이 주식회사
삼성전자주식회사
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Priority to CN201880084004.9A priority Critical patent/CN111527083A/zh
Priority to US16/954,722 priority patent/US11844271B2/en
Publication of WO2019132374A1 publication Critical patent/WO2019132374A1/ko
Priority to US18/226,363 priority patent/US20230371371A1/en

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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • An organic optoelectronic diode is an element that can switch between electrical and optical energy.
  • Organic optoelectronic devices can be roughly classified into two types according to the operating principle.
  • One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, and electrons and holes are transmitted to different electrodes to generate electrical energy, and the other is a voltage / Emitting device.
  • organic optoelectronic devices examples include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.
  • OLEDs organic light emitting diodes
  • OLEDs organic light emitting diodes
  • One embodiment provides an organic compound capable of realizing a high-efficiency and long-lived organic optoelectronic device.
  • compositions capable of implementing high-efficiency and long-lived organic optoelectronic devices.
  • Another embodiment is an organic optoelectronic device comprising the organic compound or composition 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • Another embodiment provides a display device comprising the organic opto-electronic device.
  • an organic compound represented by the following general formula (1) represented by the following general formula (1). [Chemical Formula 1]
  • ( 1) and ( 2) are each independently hydrogen, deuterium, substituted or unsubstituted
  • 030 alkyl group a substituted or unsubstituted A substituted or unsubstituted pyridinyl group, a substituted or unsubstituted thiazinyl group, a halogen, a cyano group or a combination thereof,
  • X 1 and X 2 are each independently 0 or Y, and X 1 and X 2 are, independently of each other,
  • the organic compound (first organic compound)
  • Adjacent groups are connected to each other to form a ring.
  • an organic optoelectronic device including an anode and a cathode facing each other, and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises the organic compound or the composition.
  • a display device including the organic opto-electronic device.
  • 1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.
  • &quot substituted " means that at least one hydrogen in a substituent or a compound is substituted with a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted 01 to O30 amine group, A substituted or unsubstituted 01 to 040 silyl group,
  • 030 alkyl group a 1 to 010 alkylsilyl group, a 06 to 030 arylsilyl group, a 03 to 30 cycloalkyl group, a 03 to 030 heterocycloalkyl group, a 06 to 030 aryl group, a 02 to 030 heteroaryl group, 010 trifluoroalkyl group, cyano group, or a combination thereof.
  • " substituted &quot means that at least one of the substituents or the hydrogen in the compound is deuterium, (: 1 to 030 alkyl, From 0 to 30 carbon atoms, from 0 to 30 carbon atoms, from 0 to 30 carbon atoms, from 0 to 30 carbon atoms, from 0 to 30 carbon atoms, from 0 to 30 carbon atoms, from 0 to 10 carbon atoms,
  • " substituted &quot means that at least one hydrogen in the substituent or compound is deuterium, a .20 alkyl group, a 06 to O30 aryl group,
  • a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group is A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group.
  • Substituent &quot means that at least one hydrogen in the substituent or the compound is a hydrogen atom or a group selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group,
  • substituted means that at least one hydrogen in the substituent or the compound is deuterium, (: 1 A substituted or unsubstituted aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
  • substituted &quot means that at least one Means that hydrogen is replaced by deuterium, methyl, ethyl, propanyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl or dibenzothiophenyl.
  • aryl group &quot is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital, Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, Non-aromatic fused rings fused directly or indirectly, such as a fluorenyl group, and the like.
  • the aryl group may be monocyclic, polycyclic or fused ring polycyclic (i. E.
  • heterocyclic group is a superordinate concept including a heteroaryl group, and includes N, O, S, O or S substituents in the ring compound such as an aryl group, a cycloalkyl group, a fused group thereof, S, P, and Si.
  • the heterocyclic group may contain one or more heteroatoms in whole or in each ring. have.
  • heteroaryl group &quot means that at least one heteroatom selected from the group consisting of N, O, S, P and Si is contained in the aryl group. Or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other. When the heteroaryl group is a fused ring, the ring may contain one to three heteroatoms in each ring.
  • the heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like.
  • the substituted or unsubstituted C6 to C30 aryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, A substituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o- A phenyl group, a substituted or
  • the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group , a substituted or unsubstituted oxazolyl group , a substituted or unsubstituted thiazolyl group ,
  • Substituted or unsubstituted phenanthryl groups substituted or unsubstituted phenothiazyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted dibenzofuranyl groups, or substituted or unsubstituted dibenzoyl groups, A thiophene group, or a combination thereof.
  • the hole characteristic refers to a characteristic that holes can be formed by donating electrons when an electric field is applied, and the conduction along the HOMO level 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied.
  • the electron characteristic has a conduction characteristic along the 1 < rd > 0 level and injection of electrons formed in the cathode into the light emitting layer, movement of electrons formed in the light emitting layer to the cathode, And the like.
  • the organic compound according to one embodiment is represented by the following formula (1).
  • X 1 and X 2 are each independently ⁇ or,
  • II 1 to II 8 and 11 each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted Or an unsubstituted silyl group, a substituted or unsubstituted amine group, 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • the organic compound includes pyrimidine or triazin ring, it can be a structure that is easy to receive electrons when an electric field is applied, and thus the driving voltage of the organic optoelectronic device using the organic compound can be lowered.
  • the organic compound can have a relatively high glass transition temperature by including two heteroatom-containing fused rings directly bonded thereto, thereby reducing the crystallinity of the process or driven heavy oil compound and preventing deterioration, On the other hand, the lifetime of the device to which the organic compound is applied can be improved.
  • the organic compound may have a glass transition temperature of about 50 to 3001.
  • the organic compound can be bonded directly or indirectly to the pyrimidine or triazin ring at the 3-position of the hetero atom-containing fused ring, for example, as compared with the case where it is bonded at the 1 st, 2 nd or 4 th positions of the hetero atom containing fused ring Mobility and stability can be high, thereby improving the efficiency and lifetime of a device to which an organic compound is applied
  • a device using an organic compound can realize a low driving voltage, a high efficiency and a long-life device.
  • two or three of them may be nitrogen, and the other one may be. For example, how are you? Three days.
  • mycobacteria may be nitrogen (which may be non-radioactive).
  • Examples 1 and 2 each independently represent hydrogen, deuterium, a substituted or unsubstituted 06 to O30 aryl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted
  • 1 and 2 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • the substitution may be, for example, at least one hydrogen may be substituted with deuterium, (1 to 20 alkyl, 06 to 020 aryl, pyridinyl, pyrimidinyl, triazinyl, halogen, cyano or combinations thereof , But is not limited thereto.
  • a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group may be used.
  • Eundan e.g. a combination, a substituted or unsubstituted ring 111-phenylene group, a substituted or unsubstituted! ) -Phenyl tengi, substituted or unsubstituted 0-phenyl group, a substituted or unsubstituted 111- biphenyl group, a substituted or unsubstituted I) - biphenyl group, a substituted or unsubstituted 0-biphenyl group, a substituted Or an unsubstituted 111 -terphenylene group, a substituted or unsubstituted terphenylen group, or a substituted or unsubstituted 0 -terphenylene group.
  • the substitution may be, for example, but not limited to, at least one hydrogen is deuterium, the 1-202 alkyl group, the 06-020 aryl group, the halogen, the cyano group, or a
  • a single bond a phenylene group, a biphenylenegroup, a terphenylene group, a cyano group-substituted phenylene group, a cyano group-substituted biphenylene group or a cyano group-substituted terphenylene group.
  • X 1 and X 2 may be the same or different from each other.
  • X 1 and X 2 may be 0, respectively.
  • X 1 and X 2 may be the same and may be different from X 1 , respectively.
  • X 1 and X 2 may be different from each other, X 1 is 3, X 2 is 0, or is 0 and may be 3.
  • the organic compound may be, for example, a compound represented by the formula (1) shown below according to the bonding position of the fused ring,
  • formula (1) may be represented by one of the following formula (1) depending on the bonding position between two fused rings.
  • formula (18) may be represented by one of the following formulas depending on the bonding position between two fused rings.
  • formula (10) can be represented by one of the following substituents according to the bonding position between two fused rings.
  • formula (113) may be represented by one of the following formulas (1) to (10) depending on the bonding position between two fused rings.
  • the organic compound may be, for example, selected from the compounds listed in the following Group 1, but is not limited thereto.
  • organic compounds can be applied to organic optoelectronic devices alone or together with other organic compounds.
  • organic compound When the above-mentioned organic compound is used together with other organic compounds, it can be applied in the form of a composition.
  • composition according to an embodiment may include the above-mentioned organic compound (hereinafter referred to as "first organic compound”) and organic compound having a quasi-specific property (hereinafter referred to as “second organic compound”).
  • first organic compound organic compound having a quasi-specific property
  • second organic compound organic compound having a quasi-specific property
  • the second organic compound may include, for example, a carbazole moiety, a substituted or unsubstituted carbazole compound, a substituted or unsubstituted biscarbazole compound, or a substituted or unsubstituted indolocarbazole compound, no.
  • the second organic compound may include a carbazole moiety represented by the following formula (2).
  • I 22 to 5 are each independently present or connected to each other adjacent the parent group being 22 to 25 seedlings to form a ring.
  • substitution may be such that at least one hydrogen is replaced by deuterium, the 1 to 010 alkyl group, the 6 to 12 aryl group, or the 02 to 010 heteroaryl group, , 01 acid 10 -biphenyl group, 111
  • Biphenyl 1) £ _ a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group or
  • the second organic compound may be a compound represented by the following formula (2).
  • each independently may be a single bond, a substituted or unsubstituted C6 to O30 arylthien group, a divalent substituted or unsubstituted 02 to 030 heterocyclic group, or a combination thereof,
  • III may be an integer of 0 to 2.
  • V 1 and V 2 in Formula 2 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and examples thereof include a single bond, a 111 k-phenylene group, a para-phenyl group, a size 111-biphenyl group or a para- may biphenylene group.
  • V and in the formula (2) each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted An anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted
  • a dibenzothiophenyl group a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or combinations thereof.
  • V in the formula (5) is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted dibenzofuranyl group, May be a substituted carbazole.
  • a heterocyclic group may be, for example, all hydrogen.
  • III of formula (2) may be 0 or 1, for example, 111 may be 0.
  • the bonding positions of two carbazole groups may be 2,3-bond, 3,3-bond or 2, 2-bond, and may be 3,3-bond.
  • the compound represented by the formula (2) can be represented by the formula (2) shown below. 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • the compound represented by formula (2) may be selected from among the carbazole cores listed in the following group 2 and the substituents But are not limited thereto.
  • the compound represented by the formula (2) may be one of the compounds listed in the following group 4, but is not limited thereto.
  • the second organic compound may be an indolecarbazole compound represented by a combination of the following formulas (28-1) and (2-2). 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • V each independently represent a substituted or unsubstituted 06 to 30 aryl group, a substituted or unsubstituted 02 to 030 heterocyclic group, or a combination thereof,
  • 11 3 each independently represents hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted 6 to 030 aryl group, a substituted or unsubstituted 02 to 030 heterocyclic group,
  • the remaining two * s in the formula 2 1 may each be 0 or 1 and where ⁇ and ⁇ each independently represent hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted 06 to 030 aryl group, a substituted Or an unsubstituted 02 to 030 heterocyclic group or a combination thereof.
  • V 1 and each of formulas (26-1) and (212) may be independently a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.
  • V and V in formulas (26-1) and (2-2) each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstitute
  • carbazolyl group substituted or unsubstituted fluorenyl group, or combinations thereof .
  • carbazole compound it is indole, which is represented by the combination of the formula 26-1 and 22 formula (23) - can be expressed in one and 26-6 to Chinese Language slow.
  • the compound represented by the combination of formula (2) -1 and (2 2) may be one of the compounds listed in the following group 5, but is not limited thereto.
  • First Organic Compound Task 2 Organic compounds may include various compositions by various combinations.
  • the composition may include the first organic compound, the second organic compound, in a weight ratio of about 1:99 to about 99: 1, such as about 10:90 to 90:10, about 20:80 to 80:20, about 30:70 to 70 : 30, about 40:60 to 60:40, or about 50:50.
  • the composition may further include one or more organic compounds in addition to the first organic compound problem 2 organic compound.
  • the composition may further comprise a dopant.
  • the dopant may be a red, green or blue dopant.
  • a dopant is a substance that emits light by mixing in a small amount, and a material such as a metal complex that emits light by multiple excitation, which is excited by a triplet state abnormality in general, can be used.
  • the dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.
  • the dopant may be included in an amount of about 0.1 to 20% by weight based on the total amount of the composition.
  • Examples of the dopant include a phosphorescent dopant.
  • Examples of the phosphorescent dopant include Ir, Pt, 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • the phosphorescent dopant can be, for example, a compound represented by the following formula (2), but is not limited thereto.
  • IV is silver chelate
  • n and X are the same or different from each other and are ligands which complex with ⁇ 4.
  • X and X may be, for example, bidentate ligands.
  • organic optoelectronic device to which the organic compound or composition described above is applied will be described.
  • the organic optoelectronic device may be, for example, an organic light emitting device, an organic photoelectric device, or an organic solar cell.
  • the organic optoelectronic device can be, for example, an organic light emitting device.
  • the organic optoelectronic device may include an anode and a cathode facing each other, and an organic layer positioned between the anode and the cathode, and the organic layer may include the above-described organic compound or the above-described composition.
  • the organic layer may include an active layer such as a light emitting layer or a light absorbing layer, and the above-described organic compound or the above-described composition may be included in the activity enhancement.
  • an active layer such as a light emitting layer or a light absorbing layer
  • the organic layer may include an auxiliary layer located between the anode and the active layer and / or between the cathode and the active layer, and the above-described organic compound or the above-described composition may be included in the auxiliary layer.
  • FIG. 1 is a cross-sectional view showing an example of an organic light emitting device as an example of a meta-optoelectronic device.
  • an organic light emitting device 100 includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 disposed between the anode 110 and the cathode 120 .
  • the anode 110 may be made of a high work function conductive body, for example, to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
  • the anode 110 may be formed of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; zinc oxide,
  • Metal oxides such as indium zinc oxide ( ⁇ ); (3-methylthiophene), poly (3, 4- (ethylene-1,2-dioxy) thiophene) 2: 110 and / or 3 1102 , but are not limited to, conductive polymers such as polypyrrole and polyaniline, and the like.
  • the cathode 120 may be made of a low work function conductive material, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
  • the cathode 120 may be formed of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Materials, but are not limited thereto.
  • the organic layer 105 may include the above-described organic compounds or the above-described composition.
  • the organic layer 105 may include a light emitting layer 130.
  • Emissive stimulation 130 may include the above-described organic compounds as host (s ) or the above-described compositions.
  • the light emitting layer 130 may further include another organic compound as a host.
  • the light emitting layer 130 may further include a dopant, and the dopant may be, for example, a phosphorescent dopant.
  • the organic layer 105 may include an auxiliary layer (not shown) located between the donor node 110 and the emitting layer 130 and / or between the cathode 120 and the emitting layer 130.
  • the auxiliary layer may be a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, or a combination thereof.
  • Auxiliaries may include the above-described organic compounds or the above-described compositions.
  • the organic light emitting device 200 includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 positioned between the anode 110 and the cathode 120.
  • the organic layer (10 ⁇ the light-emitting layer 2 and the cathode 120, an electron auxiliary layer (1 40) which is located between the electronic auxiliary layer 140 is for example an electron injection layer, an electron transport layer and / or hole blocking layer And the injection and transport of electrons between the cathode 120 and the light emitting layer 230 can be facilitated.
  • the above-described organic compound or the above-described composition may be included in the light emitting layer 230.
  • the light emitting layer 230 may further include another organic compound as a host.
  • the light emitting layer 230 may further include a dopant, and the dopant may be, for example, a phosphorescent dopant.
  • the above-described organic compound may be included in the electron-assisted layer 140.
  • the electron assist layer 140 may include the organic compound alone, or may be a mixture of at least two of the organic compounds described above, or may include a mixture of the organic compound and the other organic compound.
  • the organic layer 105 may further include at least one layer of a hole assist layer (not shown) positioned between the anode 110 and the light emitting layer 230.
  • the organic light emitting device described above can be applied to an organic light emitting display.
  • the intermediate 1-1 (67.5 g, 253 mmol) was dissolved in 0.8 L of 1.0 M boron tribromide solution and stirred for 5 hours. After completion of the reaction, the temperature of the reaction solution was lowered to 0 ° C, aqueous solution of thiosulfate was added dropwise for 30 minutes, then water was added, and the solution was extracted with dichloromethane (DCM), dried over magnesium sulfate anhydrous, filtered, concentrated under reduced pressure, and the obtained residue was purified by flash column chromatography Intermediate 1-2 (60.0 g, 99%) was obtained.
  • DCM dichloromethane
  • Synthesis Example 3 Synthesis of intermediate 1-3 2019/132374 1 »(: 1/10/06 018/016133
  • the intermediate 1-2 (60.0 g, 253 mmol) was dissolved in 0.3 L of N-methyl-2-pyrrolidone (NMP) in a nitrogen atmosphere, followed by addition of potassium hydroxide (70.0 g, 506 mmol) After the completion of the reaction, the solvent was distilled off and the reaction mixture was diluted with dichloromethane (DCM), water was removed with magnesium sulfate anhydrous, filtered, and the filtrate was concentrated under reduced pressure. Intermediate 1-3 (40.4 g, 73%) was obtained.
  • NMP N-methyl-2-pyrrolidone
  • the intermediate 1-3 (351-1111101) was dissolved in 0.31 (1 11101011161; 1 11 ⁇ 2 (1) ⁇ 1), and the temperature was lowered to 0 ° 0. [ '011 011117 (1 €: . (54.2 192 mmol) was placed was stirred slowly humul lower the reaction solution to FIG 0 ° C roon after 14 hours 30 minutes jujul in dichloromethane (DCM) and then water with magnesium sulfate anhydrous The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate 1-4 (55.0 & 98%).
  • DCM dichloromethane
  • Synthesis Example 33 Synthesis of Compound Host 1 2019/132374 1 » (: 1/10/06 018/016133
  • Compound Host 2 was synthesized by referring to the synthesis method of JP-A-2017-107992.
  • Compound Host 4 was synthesized by reference to the synthetic method of Korean Patent No. 10-1730779.
  • Compound Host 5 was synthesized by reference to the synthetic method of Korean Patent No. 10-1730779.
  • the compound Host 6 was synthesized by referring to the synthesis method of U.S. Patent No. 8,451,112.
  • Compound E-1 was synthesized by referring to the synthesis method of Korean Patent Publication No. 10-2014-0042630.
  • Compound No. 23 was synthesized by referring to the synthesis method of Korean Patent Laid-Open No. 10-2014-0042 0. 2019/132374 1 »(: 1/10/06 018/016133
  • Compound E-25 was synthesized by referring to the synthesis method of Korean Patent Publication No. 10-2014-0042630.
  • Compound No. 31 was synthesized by referring to the synthesis method of Korean Patent Laid-Open No. 10-2014-0042630.
  • Compound F-1 was synthesized by referring to the synthesis method of Korean Patent Publication No. 10-2014-0042630.
  • Compound F-43 was synthesized by referring to the synthesis method of Korean Patent Laid-Open Publication No. 2017-0026359.
  • Compound 58 was synthesized by referring to the synthesis method of Korean Patent Laid-Open Publication No. 2016-0048868. 2019/132374 1 »(: 1/10/06 018/016133
  • Compound F-88 was synthesized by referring to the synthesis method of Korean Patent Laid-Open Publication No. 2016-0048868.
  • the glass substrate coated with ITO (Indium tin oxide) thin film with a thickness of 1500A was washed with distilled water ultrasonic wave. After washing with distilled water, it was ultrasonically washed with isopropyl alcohol, acetone, and methanol, dried and transferred to a plasma cleaner The substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporator.
  • Compound A was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a hole injection layer having a thickness of 700 A
  • Compound B was deposited to a thickness of 50 A on top of the hole injection layer, and Compound C was deposited to a thickness of 1020 A to form a hole transport layer.
  • the organic light emitting device has a structure having five organic thin film layers, specifically, the following.
  • An organic luminescent device was prepared in the same manner as in Example 1, except that Compound 2 obtained in Synthesis Example 8 was used instead of Compound 1 as a luminescent layer host.
  • An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 3 obtained in Synthesis Example 9 was used instead of Compound 1 as a luminescent layer host.
  • An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 9 obtained in Synthesis Example 10 was used instead of Compound 1 as a light emitting layer host.
  • An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 30 obtained in Synthesis Example 21 was used instead of Compound 1 as a light emitting layer host.
  • An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 81 obtained in Synthesis Example 30 was used instead of Compound 1 as a luminescent layer host.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 121 obtained in Synthesis Example 32 was used instead of Compound 1 as a light emitting layer host.
  • An organic light emitting device was fabricated in the same manner as in Example 1, except that 4, 4 '- ( 9-0013 ⁇ 43 : 201 -9- 1) 1 1 161131 ( ⁇ 3 ⁇ 41)
  • An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 1 obtained in Synthesis Example 34 was used instead of Compound 1 as a luminescent layer host.
  • An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 13 ⁇ 43 obtained in Synthesis Example 35 was used instead of Compound 1 as a luminescent layer host.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 1 obtained in Synthesis Example 37 was used instead of Compound 1 as a light emitting layer host.
  • the voltage To 10 the current value flowing through the unit device was measured using a current-voltage meter (11 7 2400), and the measured current value was divided by the area to obtain a result.
  • the voltage To 10 ⁇ ⁇ while measuring the luminance at that time using a luminance meter (0-3000 hours).
  • the current efficiency / hour at the same current density (10 111 show / 0112) was calculated using the luminance and current density and voltage measured from the above (1) and (2).
  • Luminance (1/111 second) to 6000. (1 / e 2, and maintained at a current efficiency crossed 0 / show) by measuring the time which is reduced to 97% to obtain a result.
  • the organic light emitting devices according to Examples 1 to 8 have significantly improved driving voltage, luminous efficiency, and lifetime characteristics as compared with the organic light emitting devices according to Comparative Examples 1 to 7.
  • the glass substrate coated with ITO (Indium tin oxide) thin film with a thickness of 1500 A was washed with distilled water ultrasonic wave. After washing with distilled water, it was ultrasonically washed with isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner Next, the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporator.
  • Compound A was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a 700 A thick hole injection layer
  • Compound seeds were deposited to a thickness of 50 A on top of the hole injection layer, and Compound C was deposited to a thickness of 1020 A to form a hole transport layer.
  • Compound 1 obtained in Synthesis Example 7 and Synthesis Example Compound E-31 obtained in Example 42 was simultaneously used as a host, 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • the tris (2 - phenylpyridine) iridium (III) [11] [3] was doped with 10% Then, compound 1 and compound 31 were used in a weight ratio of 3: 7. Subsequently, a compound layer and an electron transport layer were simultaneously vacuum-deposited at a ratio of 1: 1 to form an electron transport layer having a thickness of 300 nm.
  • the organic light emitting device was fabricated by forming a cathode by sequentially vacuum-depositing 3 ⁇ 4 and 1200 persons.
  • the organic light emitting device has a structure having five organic thin film layers. Specifically, the organic light emitting device has the following structure.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 3 obtained in Synthesis Example 9 was used instead of Compound 1.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 46 obtained in Synthesis Example 24 was used instead of Compound 1. 2019/132374 1 »(: 1 ⁇ 1 ⁇ 2018/016133
  • An organic light emitting device was fabricated in the same manner as in Example 9, except that Compound 81 obtained in Synthesis Example 30 was used instead of Compound 1.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 121 obtained in Synthesis Example 32 was used instead of Compound 1.
  • An organic luminescent device was fabricated in the same manner as in Example 10, except that Compound 1 obtained in Synthesis Example 39 was used instead of Compound Emulsion-31.
  • An organic luminescent device was fabricated in the same manner as in Example 10, except that the compound shown in the synthesis example 41 was used in place of the compound seedlings-31.
  • An organic light emitting device was prepared in the same manner as in Example 10, except that the compound 1 & tilde &
  • An organic light emitting device was fabricated in the same manner as in Example 9, except that Compound 31 was used alone as a light emitting layer host.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound (3) 1) obtained in Synthesis Example 33 was used instead of Compound (1).
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 2 obtained in Synthesis Example 34 was used instead of Compound 1.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 13 ⁇ 43 obtained in Synthesis Example 35 was used instead of Compound 1.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 4 obtained in Synthesis Example 36 was used instead of Compound 1.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that Compound 5 obtained in Synthesis Example 37 was used instead of Compound 1.
  • An organic light emitting device was fabricated by the same method as in Example 9, except that the compound 1 ⁇ 6 obtained in Synthesis Example 38 was used instead of the Compound 1. 14, the driving voltage, the luminous efficiency and the lifetime characteristics of the organic light emitting device were evaluated.
  • the driving voltage, the luminous efficiency, and the lifetime characteristics are remarkably improved.

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Abstract

화학식 1로 표현되는 유기 화합물, 조성물, 유기광전자소자 및 표시 장치에 관한 것이다.

Description

【명세세
【발명의 명칭】
유기 화합물,조성물,유기 광전자소자및표시 장치
【기술분야】
유기 화합물，조성물,유기 광전자소자및표시 장치에 관한것이다.
【배경기술】
유기 광전자소자 (organic optoelectronic diode)는전기 에너지와광에너지를 상호전환할수있는소자이다.
유기 광전자소자는동작원리에 따라크게두가지로나눌수있다. 하나는 광에너지에 의해 형성된 엑시톤 (exciton)이 전자와정공으로분리되고전자와 정공이 각각다른전극으로전달되면서 전기 에너지를발생하는광전소자이고, 다른하나는전극에 전압또는전류를공급하여 전기 에너지로부터 광에너지를 발생하는발광소자이다.
유기 광전자소자의 예로는유기 광전소자,유기 발광소자,유기 태양전지 및유기 감광체드럼 (organic photo conductor drum)등을들수있다.
이 중,유기 발광소자 (organic light emiting diode, OLED)는근래평관표시 장치 (flat panel display device)의수요증가에 따라크게주목받고있다.유기 발광 소자는전기 에너지를빛으로전환시키는소자로서，유기 발광소자의 성능은전극 사이에위치하는유기 재료에 의해 많은영향을받는다.
【발명의상세한설명】
【기술적 과제】
일구현예는고효율및장수명 유기 광전자소자를구현할수있는유기 화합물을제공한다.
다른구현예는고효율및장수명 유기 광전자소자를구현할수있는 조성물을제공한다.
또다른구현예는상기유기 화합물또는조성물을포함하는유기 광전자 2019/132374 1»（：1^1{2018/016133
2 소자를제공한다.
또다른구현예는상기유기 광전자소자를포함하는표시 장치를제공한다. 【기술적 해결방법】
일구현예에 따르면，하기 화학식 1로표현되는유기 화합물을제공한다. [화학식 1]
Figure imgf000003_0001
상기 화학식 1에서,
7}내지 2：3는각각독립적으로
Figure imgf000003_0002
이고,
7}내지 7}중적어도둘은 X이고，
사1및사2는각각독립적으로수소,중수소,치환또는비치환된（그1내지
030알킬기,치환또는비치환된
Figure imgf000003_0003
030아릴기,치환또는비치환된 피리디닐기,치환또는비치환된피리미디닐기,치환또는비치환된트리아지닐기， 할로겐,시아노기또는이들의조합이고，
은단일결합또는치환또는비치환된 6내지 020아릴렌기이고， X1및 X2는각각독립적으로 0또는요이고，
Figure imgf000003_0004
독립적으로수소,중수소,치환또는비치환된 01 내지 030알킬기，치환또는비치환된 06내지 030 6ᅵ_릴기，치환또는비치환된 03 내지 030헤테로고리기,치환또는비치환된실릴기,치환또는비치환된아민기， 할로겐,시아노기또는이들의조합이다.
다른구현예에 따르면,상기 유기 화합물（제 1유기 화합물）및하기 화학식
2로표현되는카바졸모이어티를포함하는제 2유기 화합물을포함하는조성물을 제공한다. 2019/132374 1»（：1/10公018/016133
3
[화학식 2]
Figure imgf000004_0001
상기 화학식 2에서,
은단일 결합，치환또는비치환된 C6내지 030아릴렌기또는 2가의 치환또는비치환된 02내지 030헤테로고리기이고,
은치환또는비치환된 06내지 30아릴기또는치환또는비치환된 02 내지 030헤테로고리기이고，
Figure imgf000004_0002
독립적으로수소，중수소,치환또는비치환된 01내지 020알킬기，치환또는비치환된 06내지 030아릴기또는치환또는비치환된 02내지 030헤테로고리기이고，
Figure imgf000004_0003
인접한기끼리 연결되어 고리를형성한다.
또다른구현예에 따르면,서로마주하는애노드와캐소드,그리고상기 애노드와상기 캐소드사이에 위치하는유기층을포함하고，상기 유기층은상기 유기 화합물또는상기조성물을포함하는유기 광전자소자를제공한다.
또다른구현예에 따르면,상기 유기 광전자소자를포함하는표시 장치를 제공한다.
【유리한효과】
고효율장수명유기 광전자소자를구현할수있다.
【도면의 간단한설명】
도 1및도 2는각각일구현예에 따른유기 발광소자를도시한단면도이다. 【발명의실시를위한최선와형태】
이하，본발명의 구현예를상세히 설명하기로한다. 다만,이는예시로서 2019/132374 1»（：1^1{2018/016133
4 제시되는것으로,이에 의해본발명이 제한되지는않으며 본발명은후술할 청구범위의 범주에 의해정의될뿐이다.
본명세서에서 ’’치환”이란별도의 정의가없는한,치환기 또는화합물중의 적어도하나의수소가중수소,할로겐기 ,히드록실기,아미노기 ,치환또는비치환된 01내지 030아민기，니트로기，치환또는비치환된 01내지 040실릴기,（그1내지
030알킬기，〔1내지 010알킬실릴기, 06내지 030아릴실릴기， 03내지 30 시클로알킬기， 03내지 030헤테로시클로알킬기， 06내지 030아릴기, 02내지 030 헤테로아릴기,（ 내지 020
Figure imgf000005_0001
010트리플루오로알킬기，시아노기, 또는이들의조합으로치환된것을의미한다.
본발명의 일 예에서，”치환”은치환기또는화합물중의 적어도하나의 수소가중수소，（：1내지 030알킬기,
Figure imgf000005_0002
내지 010알킬실릴기, 06내지 030 아릴실릴기， 03내지 030시클로알킬기, 03내지 030헤테로시클로알킬기， 06내지 030아릴기, 2내지 030헤테로아릴기로치환된 것을의미한다. 또한，본발명의 구체적인일 예에서，”치환”은치환기 또는화합물중의 적어도하나의 수소가 중수소, 내지。20알킬기, 06내지 030아릴기，또는 02내지 030
헤테로아릴기로치환된것을의미한다.또한，본발명의 구체적인 일 예에서，
"치환”은치환기 또는화합물중의 적어도하나의수소가중수소시내지 05 알킬기， 06내지 018아릴기,피리디닐기,퀴놀리닐기,이소퀴놀리닐기，
디벤조퓨란일기,디벤조티오펜일기또는카바졸일기로치환된것을의미한다.또한， 본발명의구체적인일 예에서，"치환”은치환기 또는화합물중의 적어도하나의 수소가중수소，（：1내지 05알킬기,〔6내지 018아릴기，디벤조퓨란일기또는 디벤조티오펜일기로치환된것을의미한다.또한,본발명의 구체적인 일 예에서， "치환”은치환기 또는화합물중의 적어도하나의 수소가중수소，메틸기，에틸기, 프로판일기，부틸기,페닐기,바이페닐기,터페닐기,나프틸기,트리페닐기, 디벤조퓨란일기 또는디벤조티오펜일기로치환된것을의미한다.
본명세서에서 ”헤테로”란별도의 정의가없는한,하나의 작용기 내에此0, S，P및 Si로이루어진군에서 선택되는헤테로원자를 1내지 3개함유하고， 나머지는탄소인것을의미한다.
본명세서에서 "아릴 (aryl)기”는탄화수소방향족모이어티를하나이상갖는 그룹을총괄하는개념으로서,탄화수소방향족모이어티의 모든원소가 p-오비탈을 가지면서,이들 p-오비탈이 공액 (conjugation)을형성하고있는형태,예컨대페닐기， 나프틸기등을포함하고， 2이상의 탄화수소방향족모이어티들이 시그마결합을 통하여 연결된형태,예컨대바이페닐기,터페닐기,쿼터페닐기 등을포함하며， 2 이상의 탄화수소방향족모이어티들이 직접 또는간접적으로융합된비방향족융합 고리，예컨대플루오레닐기등을포함할수있다.
아릴기는모노시클릭,폴리시클릭 또는융합고리 폴리시클릭 (즉,
탄소원자들의 인접한쌍들을나눠 가지는고리)작용기를포함한다.
본명세서에서 "헤테로고리기 (heterocyclic group)"는헤테로아릴기를포함하는 상위 개념으로서，아릴기,시클로알킬기,이들의 융합고라또는이들의조합과같은 고리 화합물내에 탄소 (C)대신 N, O, S, P및 Si로이루어진군에서선택되는 헤테로원자를적어도한개를함유하는것을의미한다.상기 헤테로고리기가 융합고리인경우,상기 헤테로고리기 전체또는각각의 고리마다헤테로원자를한 개 이상포함할수있다.
일 예로 "헤테로아릴 (heteroaryl)기”는아릴기 내에 N, O, S, P및 Si로이루어진 군에서선택되는헤테로원자를적어도한개를함유하는것을의미한다 .2이상의 헤테로아릴기는시그마결합을통하여 직접 연결되거나，상기 헤테로아릴기가 2 이상의고리를포함할경우, 2이상의 고리들은서로융합될수있다. 상기 헤테로아릴기가융합고리인경우,각각의 고리마다상기 헤테로원자를 1내지 3개 포함할수있다.
상기 헤테로고리기는구체적인예를들어，피리디닐기，피리미디닐기, 피라지닐기，피리다지닐기，트리아지닐기,퀴놀리닐기，이소퀴놀리닐기 등을포함할 수있다. 보다구체적으로,치환또는비치환된 C6내지 C30아릴기는치환또는 비치환된페닐기，치환또는비치환된나프틸기，치환또는비치환된안트라세닐기， 치환또는비치환된페난트레닐기,치환또는비치환된나프타세닐기,치환또는 비치환된피레닐기,치환또는비치환된바이페닐기,치환또는비치환된 p-터페닐기， 치환또는비치환된 m-터페닐기,치환또는비치환된 o-터페닐기,치환또는
비치환된크리세닐기，치환또는비치환된트리페닐렌기，치환또는비치환된 페릴레닐기,치환또는비치환된플루오레닐기，치환또는비치환된인데닐기또는 이들의조합일수있으나，이에 제한되지는않는다.
보다구체적으로，치환또는비치환된 C2내지 C30헤테로고리기는치환 또는비치환된퓨라닐기,치환또는비치환된티오페닐기,치환또는비치환된 피롤릴기,치환또는비치환된피라졸릴기，치환또는비치환된이미다졸일기,치환 또는비치환된트리아졸일기,치환또는비치환된옥사졸일기,치환또는비치환된 티아졸일기,치환또는비치환된옥사디아졸일기,치환또는비치환된
티아디아졸일기，치환또는비치환된피리딜기,치환또는비치환된피리미디닐기， 치환또는비치환된피라지닐기，치환또는비치환된트리아지닐기，치환또는 비치환된벤조퓨라닐기 ,치환또는비치환된벤조티오페닐기，치환또는비치환된 벤즈이미다졸일기，치환또는비치환된인돌일기，치환또는비치환된퀴놀리닐기 , 치환또는비치환된이소퀴놀리닐기，치환또는비치환된퀴나졸리닐기，치환또는 비치환된퀴녹살리닐기,치환또는비치환된나프티리디닐기，치환또는비치환된 벤즈옥사진일기，치환또는비치환된벤즈티아진일기，치환또는비치환된
아크리디닐기,치환또는비치환된페나진일기,치환또는비치환된페노티아진일기， 치환또는비치환된페녹사진일기,치환또는비치환된디벤조퓨란일기，또는치환 또는비치환된디벤조티오펜일기또는이들의조합일수있으나,이에 제한되지는 않는다.
본명세서에서,정공특성이란,전기장 (electric field)을가했을때 전자를 공여하여 정공을형성할수있는특성을말하는것으로, HOMO준위를따라전도 2019/132374 1»（：1^1{2018/016133
7 특성을가져 양극에서 형성된정공의 발광층으로의주입,발광층에서 형성된정공의 양극으로의 이동및발광층에서의 이동을용이하게하는특성을의미한다.
또한전자특성이란，전기장을가했을때 전자를받을수있는특성을말하는 것으로, 1乂1 0준위를따라전도특성을가져 음극에서 형성된전자의 발광층으로의 주입,발광층에서 형성된전자의 음극으로의 이동및발광층에서의 이동을용이하게 하는특성을의미한다.
이하일구현예에 따른유기 화합물을설명한다.
일구현예에 따른유기 화합물은하기 화학식 1로표현된다.
[화학식 1]
Figure imgf000008_0001
내지 å3중적어도둘은 ^이고,
사1및쇼戶는각각독립적으로수소,중수소，치환또는비치환된（：1내지 030알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 피리디닐기,치환또는비치환된피리미디닐기,치환또는비치환된트리아지닐기, 할로겐,시아노기또는이들의조합이고,
느은단일결합또는치환또는비치환된 06내지 020아릴렌기이고,
X1및 X2는각각독립적으로◦또는 이고，
II1내지 II8및 11는각각독립적으로수소，중수소,치환또는비치환된€1 내지 030알킬기,치환또는비치환된 6내지 030아릴기,치환또는비치환된 03 내지 030헤테로고리기，치환또는비치환된실릴기,치환또는비치환된아민기, 2019/132374 1»（：1^1{2018/016133
8 할로겐,시아노기또는이들의조합이다.
유기 화합물은피리미딘또는트리아진고리를포함함으로써 전기장인가시 전자를받기 쉬운구조가될수있고，이에 따라유기 화합물을적용한유기 광전자 소자의구동전압을낮출수있다.
또한유기 화합물은직접 결합된 2개의 헤테로원자함유융합고리를 포함함으로써 비교적높은유리전이온도를가질수있고이에 따라공정 또는구동 중유기 화합물의 결정성을줄이고열화를방지하여유기 화합물의 열적 안정성을 도모하는한편유기 화합물을적용한소자의 수명을개선할수있다.일 예로，유기 화합물은약 50내지 3001：의유리전이온도를가질수있다.
또한유기 화합물은헤테로원자함유융합고리의 3번위치에서 피리미딘 또는트리아진고리와직접 또는간접적으로결합함으로써 예컨대헤테로원자함유 융합고리의 1번， 2번또는 4번위치에서 결합한경우와비교하여 전하의 이동성 및 안정성이높을수있고이에 따라유기 화합물을적용한소자의 효율및수명을 개선할수있다
따라서유기 화합물을적용한소자는낮은구동전압，높은효율및 장수명 소자를구현할수있다.
일 예로， 내지안중둘은질소어）이고나머지 하나는이일수있다. 예컨대方및 는질소이고 는 ?3일수있다.
예컨대 7}및方는질소이고 은 0?"일수있다.
예컨대 å1및 는질소이고
Figure imgf000009_0001
있다.
일 예로， 내지균은각각질소（비일수있다.
일 예로，사1및 2는각각독립적으로수소,중수소，치환또는비치환된 06 내지 030아릴기，치환또는비치환된피리디닐기,치환또는비치환된
피리미디닐기,치환또는비치환된트리아지닐기 또는이들의 조합일수있다. 예컨대 1및 2는각각독립적으로치환또는비치환된페닐기，치환또는 비치환된바이페닐기，치환또는비치환된터페닐기,치환또는비치환된나프틸기， 2019/132374 1»（：1^1{2018/016133
9 치환또는비치환된트리페닐레닐기,치환또는비치환된피리디닐기，치환또는 비치환된피리미디닐기또는치환또는비치환된트리아지닐기일수있다. 여기서 치환은예컨대적어도하나의 수소가중수소，（：1내지€20알킬기, 06내지 020 아릴기，피리디닐기，피리미디닐기,트리아지닐기，할로겐,시아노기또는이들의 조합으로치환된것일수있으나，이에 한정되는것은아니다.
일 예로，느은단일 결합，치환또는비치환된페닐텐기，치환또는비치환된 바이페닐렌기또는치환또는비치환된터페닐렌기일수있다.
예컨대 은단일결합,치환또는비치환된 111-페닐렌기，치환또는비치환된 !）-페닐텐기 ,치환또는비치환된 0 -페닐렌기 ,치환또는비치환된 111-바이페닐렌기， 치환또는비치환된 I）-바이페닐렌기 ,치환또는비치환된 0 -바이페닐렌기 ,치환또는 비치환된 111-터페닐렌기,치환또는비치환된 터페닐텐기또는치환또는비치환된 0 -터페닐렌기일수있다. 여기서 치환은예컨대 적어도하나의수소가중수소,（그1 내지 020알킬기， 06내지 020아릴기,할로겐,시아노기 또는이들의조합으로 치환된것일수있으나，이에 한정되는것은아니다.
예컨대느은단일결합,페닐렌기,바이페닐텐기,터페닐렌기,시아노기 치환된 페닐렌기,시아노기 치환된바이페닐렌기또는시아노기 치환된터페닐렌기일수 있다.
일 예로， X1과 X2는서로같거나다를수있다.
예컨대 과 는같을수있고 X1과 X2는각각 0일수있다.
예컨대 X1과 X2는같을수있고 X1과 는각각 일수있다.
예컨대 X1과 X2는서로다를수있고 X1은 3이고 X2는 0이거나 은 0이고 는 3일수있다.
유기 화합물은융합고리의 결합위치에 따라예컨대하기 화학식 1쇼내지
1£）중어느하나로표현될수있다. 2019/132374 1»（：1^1{2018/016133
1 0
［화학식 1시
Figure imgf000011_0001
［화학식 1이
Figure imgf000011_0002
상기화학식 1요내지 II）에서，方내지 1,쇼2,ᄂ X1， X2,모1내지묘8은 전술한바와같다. 2019/132374 1»（：1^1{2018/016133
1 1 일 예로，화학식 1쇼는 2개의융합고리사이의 결합위치에 따라예컨대 하기 화학식 1쇼（1중어느하나로표현될수있다.
［화학식 1쇼리
Figure imgf000012_0002
［화학식 1쇼이
Figure imgf000012_0001
2019/132374 1»（：1^1{2018/016133
12
［화학식 1쇼¾
상
Figure imgf000013_0001
내지 , 1,쇼1·2,ᄂ넜，；#，: 내지 II8은 전술한바와같다.
예컨대,화학식
Figure imgf000013_0002
표현될수있다.
일 예로，화학식 18는 2개의 융합고리사이의 결합위치에 따라예컨대하기 화학식 내（1중어느하나로표현될수있다.
［화학식 \3&］
Figure imgf000013_0003
2019/132374 1»（：1/10公018/016133
13
[화학식 1미＞]
Figure imgf000014_0002
상기 화학식
Figure imgf000014_0001
내1에서，方내지 ， 1， 2,ᄂ X1， X2, II1내지 II8은 \ 02019/132374 1»（：1/10公018/016133
14 전술한바와같다.
예컨대,화학식 내는 163또는 1해로표현될수있다.
일 예로,화학식 10는 2개의 융합고리사이의 결합위치에 따라예컨대하기 화학식 \€ &내지 代犯중어느하나로표현될수있다.
[화학식 103]
Figure imgf000015_0002
[화학식 100]
Figure imgf000015_0001
2019/132374 1»（：1/10公018/016133
15
[화학식 10(1]
Figure imgf000016_0001
전술한바와같다.
일 예로，화학식 113는 2개의 융합고리사이의 결합위치에 따라예컨대하기 화학식 1 내지 10(1중어느하나로표현될수있다.
[화학식 103]
Figure imgf000016_0002
2019/132374 1»(：1^1{2018/016133
1 6
［화학식 1에
Figure imgf000017_0002
상기 화학식 1 내지 1어에서，方내지公， 1, 2,ᄂ X1， X2,모1내지 II8은 전술한바와같다.
유기 화합물은예컨대하기그룹 1에 나열된화합물에서선택된하나일수 있으나，이에 한정되는것은아니다.
［그룹 1］
Figure imgf000017_0001
Figure imgf000018_0001
18
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
2019/132374 1»（：1^1{2018/016133
24
Figure imgf000025_0001
전술한유기 화합물은단독으로또는다른유기 화합물과함께유기 광전자 소자에 적용될수있다. 전술한유기 화합물이 다른유기 화합물과함께사용되는 경우,조성물의 형태로적용될수있다.
이하일구현예에 따른조성물을설명한다.
일구현예에 따른조성물은전술한유기 화합물（이하“제 1유기 화합물”이라 한다）와정공특성을가지는유기화합물（이하“제 2유기 화합물”이라한다）을 포함할수있다.
제 2유기 화합물은예컨대카바졸모이어티를포함할수있고예컨대치환 또는비치환된카바졸화합물,치환또는비치환된비스카바졸화합물또는치환 또는비치환된인돌로카바졸화합물일수있으나,이에 한정되는것은아니다. 일 예로，제 2유기 화합물은예컨대하기 화학식 2로표현되는카바졸 모이어티를포함할수있다.
[화학식 2]
Figure imgf000025_0002
상기 화학식 2에서，
은단일결합，치환또는비치환된 C6내지 030아릴렌기또는 2가의 치환또는비치환된 02내지 030헤테로고리기이고,
은치환또는비치환된 06내지 030아릴기 또는치환또는비치환된 02 내지 30헤테로고리기이고, 2019/132374 1»（：1^1{2018/016133
25
Figure imgf000026_0001
독립적으로수소,중수소,치환또는비치환된 01내지 020알킬기,치환또는비치환된 06내지 030아릴기 또는치환또는비치환된 02내지 030헤테로고리기이고，
요22내지 5는각각독립적으로존재하거나모22내지묘25중인접한기끼리 연결되어 고리를형성한다.
일 예로화학식 2의 정의에서，치환은적어도하나의수소가중수소,（그1내지 010알킬기， 6내지 012아릴기또는 02내지 010헤테로아릴기로치환된것일수 있고,예컨대 적어도하나의 수소가중수소,페닐기, 01산10 -바이페닐기， 111
바이페닐기, 1）£ _바이페닐기,터페닐기,나프틸기，디벤조퓨란일기또는
디벤조티오펜일기로치환된것일수있다.
일 예로,제 2유기 화합물은하기 화학식 2쇼로표현되는화합물일수있다. ［화학식 2시
Figure imgf000026_0003
상기 화학식 2쇼에서,
및 는각각독립적으로단일결합，치환또는비치환된 C6내지 030 아릴텐기， 2가의 치환또는비치환된 02내지 030헤테로고리기 또는이들의조합일 수있고,
및 는각각독립적으로치환또는비치환된 06내지 030아릴기，치환 또는비치환된 02내지 030헤테로고리기또는이들의 조합일수있고,
Figure imgf000026_0002
독립적으로수소,중수소,치환또는 비치환된 01내지 020알킬기，치환또는비치환된 06내지 030아릴기,치환또는 비치환된 02내지 030헤테로고리기 또는이들의조합일수있고， 2019/132374 1»（：1^1{2018/016133
26
III은 0내지 2의 정수일수있다.
일 예로，화학식 2쇼의 V1및 는각각독립적으로단일결합，치환또는 비치환된페닐렌기또는치환또는비치환된바이페닐렌기일수있고，예컨대단일 결합, 111 크 -페닐렌기， para-페닐렌기， 111 크-바이페닐렌기 또는 para-바이페닐렌기일수 있다.
일 예로,화학식 2쇼의 V및 는각각독립적으로치환또는비치환된 페날기，치환또는비치환된바이페닐기，치환또는비치환된터페닐기，치환또는 비치환된나프틸기，치환또는비치환된안트라세닐기，또는치환또는비치환된 트리페닐텐기,치환또는비치환된피리디닐기,치환또는비치환된
디벤조티오펜일기，치환또는비치환된디벤조퓨란일기，치환또는비치환된 카바졸일기，치환또는비치환된플루오레닐기또는이들의 조합일수있다.
예컨대화학식 5쇼의 V및 는각각독립적으로치환또는비치환된페닐기,치환 또는비치환된바이페닐기,치환또는비치환된디벤조티오펜일기，치환또는 비치환된디벤조퓨란일기또는치환또는비치환된카바졸일기일수있다.
일 예로，화학식
Figure imgf000027_0001
，치환또는 비치환된 06내지 030아릴기또는치환또는비치환된 02내지 030
헤테로고리기일수있고，예컨대모두수소일수있다.
일 예로,화학식 2쇼의 III은 0또는 1일수있고，예컨대 111은 0일수있다. 일 예로,화학식 2쇼에서두개의 카바졸기의 결합위치는 2, 3 -결합， 3, 3 -결합 또는 2, 2 -결합일수있으며,예컨대 3, 3 -결합일수있다.
일 예로，화학식 2쇼로표현되는화합물은하기 화학식 2쇼-1로표현될수 있다. 2019/132374 1»（：1^1{2018/016133
27
[화학식 2쇼-1]
Figure imgf000028_0001
전술한 바와같다.
일 예로，화학식 2쇼로표현되는화합물은하기 그룹 2에 나열된카바졸코어 중하나와하기 그룹 3에 나열된치환기
Figure imgf000028_0002
조합한화합물일수 있으나，이에 한정되는것은아니다.
[그룹 2]
Figure imgf000028_0003
2019/132374 1»（：1/10公018/016133
28
[그룹 3]
Figure imgf000029_0001
그룹 2및 3에서，*는연결지점이다.
일 예로,화학식 2쇼로표현되는화합물은예컨대하기 그룹 4에 나열된 화합물중하나일수있으나,이에 한정되는것은아니다.
[그룹 4]
[£-1] ^-2] [£-3] [£-4] -5]
Figure imgf000029_0002
[E-l 1] [E-12] [E-13] [E-14] [E-15]
Figure imgf000030_0001
Figure imgf000031_0001
[E-66] [E-67] [E-68] [E-69] [E-70]
Figure imgf000032_0001
[E-96] [E-97] [E-98] [E-99] [E-100]
Figure imgf000033_0001
2019/132374 （그1/10公018/016133
33
Figure imgf000034_0001
일 예로,제 2유기 화합물은하기 화학식 28-1과 2 2의조합으로표현되는 인돌로카바졸화합물일수있다. 2019/132374 1»（：1^1{2018/016133
34
[화학식 26-1] [화학식 26-2]
Figure imgf000035_0001
및 은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기 , 2가의 치환또는비치환된 02내지 030헤테로고리기 또는이들의 조합일수있고,
V및 은각각독립적으로치환또는비치환된 06내지〔30아릴기，치환 또는비치환된 02내지 030헤테로고리기또는이들의조합일수있고,
Figure imgf000035_0002
113()은각각독립적으로수소，중수소，치환또는 비치환된 01내지 020알킬기,치환또는비치환된€6내지 030아릴기，치환또는 비치환된 02내지 030헤테로고리기또는이들의조합일수있고，
화학식 2 의 인접한두개의 *는화학식 2묘-2의 두개의 *와결합할 수있고,
화학식 2 1의 나머지 두개의 *는각각 0^및대 일수있고,여기서 ^ 및 ^는각각독립적으로수소,중수소,치환또는비치환된 01내지 020알킬기, 치환또는비치환된 06내지 030아릴기,치환또는비치환된 02내지 030 헤테로고리기또는이들의 조합일수있다.
일 예로，화학식 26-1및 212의 V1및 는각각독립적으로단일결합, 치환또는비치환된페닐렌기또는치환또는비치환된바이페닐렌기일수있다. 일 예로,화학식 26-1 및 2모-2의 V및 는각각독립적으로치환또는 비치환된페닐기,치환또는비치환된바이페닐기,치환또는비치환된터페닐기, 치환또는비치환된나프틸기 ,치환또는비치환된안트라세닐기 ,또는치환또는 비치환된트리페닐렌기,치환또는비치환된피리디닐기，치환또는비치환된 디벤조티오펜일기，치환또는비치환된디벤조퓨란일기,치환또는비치환된 2019/132374 1»（：1^1{2018/016133
35 카바졸일기,치환또는비치환된플루오레닐기또는이들의조합일수있다. 일 예로，화학식 26-1 및 2 2의조합으로표현되는인돌로카바졸화합물은 하기 화학식 23 -&내지 26-6중어느하나로표현될수있다.
［화학식 2B-a］ ［화학식 26^］ ［화학식 26-0］
Figure imgf000036_0003
상기 화학식
Figure imgf000036_0001
전술한바와같다.
일 예로，화학식 2묘-1과 2 2의조합으로표현되는화합물은예컨대하기 그룹 5에 나열된화합물중하나일수있으나，이에 한정되는것은아니다.
［그룹 5］
케 -2] ^-3] 케 [ -5]
Figure imgf000036_0002
Figure imgf000037_0001
[F-31] [F-32] [F-33] [F-34] [F-35]
Figure imgf000038_0001
Figure imgf000039_0001
10
Figure imgf000039_0002
p-86] [F-87] [F-88] [F-89] [F-90]
Figure imgf000040_0001
제 1유기 화합물과제 2유기 화합물은다양한조합에 의해다양한조성물을 포함할수있다. 조성물은제 1유기 화합물과제 2화합물을약 1:99내지 99:1의 중량비로포함할수있으며，예컨대 약 10:90내지 90:10,약 20:80내지 80:20,약 30:70내지 70:30,약 40:60내지 60:40또는약 50:50의 중량비로포함할수있다. 조성물은제 1유기 화합물과제 2유기 화합물외에 1종이상의 유기 화합물을더포함할수있다.
조성물은도펀트를더 포함할수있다. 도펀트는적색，녹색또는청색 도펀트일수있다. 도펀트는미량혼합되어 발광을일으키는물질로，일반적으로 삼중항상태 이상으로여기시키는다중항여기 (multiple excitation)에 의해발광하는 금속착체 (metal complex)와같은물질이사용될수있다. 상기 도펀트는예컨대 무기，유기，유무기 화합물일수있으며， 1종또는 2종이상포함될수있다.
도펀트는조성물의 총함량에 대하여 약 0.1내지 20중량%로포함될수있다. 도펀트의 일 예로인광도펀트를들수있으며，인광도펀트의 예로는 Ir, Pt, 2019/132374 1»（：1^1{2018/016133
40
Figure imgf000041_0001
조합을포함하는유기 금속화합물을들수있다.인광도펀트는예컨대하기 화학식 2로표현되는 화합물을사용할수있으나,이에 한정되는것은아니다.
［화학식 ¾
1 ᆻ故
상기 화학식 2；에서, IV!은금속이고,느및 X는서로같거나다르며 ^4과 착화합물을형성하는리간드이다.
Figure imgf000041_0002
이들의조합일수있고,상기느및 X는예컨대바이덴테이트리간드일수있다. 이하전술한유기 화합물또는조성물을적용한유기 광전자소자를 설명한다.
유기 광전자소자는예컨대유기 발광소자，유기 광전소자또는유기 태양 전지 등일수있다. 유기 광전자소자는일 예로유기 발광소자일수있다. 유기 광전자소자는서로마주하는애노드와캐소드，그리고애노드와캐소드 사이에 위치하는유기층을포함할수있고，유기층은전술한유기 화합물또는 전술한조성물을포함할수있다.
유기층은발광층또는흡광층과같은활성층을포함할수있고,전술한유기 화합물또는전술한조성물은활성증에 포함될수있다.
유기층은애노드와활성층사이 및/또는캐소드와활성층사이에 위치하는 보조층을포함할수있고,전술한유기 화합물또는전술한조성물은보조층에 포함될수있다.
도 1은유기 광전자소자의 일 예인유기 발광소자의 일 예를보여주는 단면도이다.
도 1을참고하면，일구현예에 따른유기 발광소자 (100)는서로마주하는 애노드 (110)와캐소드 (120),그리고애노드 (110)와캐소드 (120)사이에 위치하는 유기층 (105)을포함한다. 2019/132374 1»（：1^1{2018/016133
41 애노드 (110)는예컨대정공주입이 원활하도록일함수가높은도전체로 만들어질수있으며,예컨대금속,금속산화물및/또는도전성 고분자로만들어질 수있다. 애노드 (110)는예컨대니켈,백금，바나둠，크롬，구리，아연，금과같은 금속또는이들의 합금;아연산화물,인둠산화물,인둠주석산화물 ( 0),
인듐아연산화물 (¾◦)과같은금속산화물; 2：110와 또는 31102와 와같은금속과 산화물의조합;폴리 (3 -메틸티오펜),폴리 (3, 4-(에틸렌- 1,2- 디옥시)티오펜 )(?01＞년 16116(¾0표＞1：1^0^)116116: 묘!)。!)，폴리피롤및폴리아닐린과같은 도전성고분자등을들수있으나,이에 한정되는것은아니다.
캐소드 (120)는예컨대 전자주입이 원활하도록일함수가낮은도전체로 만들어질수있으며，예컨대금속,금속산화물및/또는도전성 고분자로만들어질 수있다. 캐소드 (120)은예컨대마그네슘,칼슘，나트륨，칼륨，타이타늄，인둠, 이트륨,리튬，가돌리늄，알루미늄,은,주석，납,세슘,바륨등과같은금속또는 이들의 합금;
Figure imgf000042_0001
물질을들 수있으나，이에 한정되는것은아니다.
유기층 (105)은전술한유기 화합물또는전술한조성물을포함할수있다. 유기층 (105)은발광층 (130)을포함할수있다.
발광증 (130)은호스트 (1108†;)로서 전술한유기 화합물또는전술한조성물을 포함할수있다. 발광층 (130)은호스트로서또다른유기 화합물을더 포함할수 있다. 발광층 (130)은도펀트를더포함할수있고도펀트는예컨대 인광도펀트일 수있다.
유기층 (105)은애노드 (110)와발광층 (130)사이 및/또는캐소드 (120)와 발광층 (130)사이에 위치하는보조층 (도시하지 않음)을더 포함할수있다.
보조층은정공주입층,정공수송층，전자차단층，전자주입층，전자수송층，정공 차단증또는이들의조합일수있다. 보조증은전술한유기 화합물또는전술한 조성물을포함할수있다.
도 2는다른구현예에 따른유기 발광소자의 단면도이다. 2019/132374 1»（：1^1{2018/016133
42 도 2를참고하면,일구현예에 따른유기 발광소자 (200)는서로마주하는 애노드 (110)와캐소드 (120),그리고애노드 (110)와캐소드 (120)사이에 위치하는 유기층 (105)을포함한다.
유기층 (10句은발광층 (2 )과캐소드 (120)사이에 위치하는전자보조층 (140)을 포함한다. 전자보조층 (140)은예컨대 전자주입층,전자수송층및/또는정공 차단층일수있으며,캐소드 (120)와발광층 (230)사이의 전자의주입 및 이동을 용이하게할수있다.
일 예로，전술한유기 화합물또는전술한조성물은발광층 (230)에 포함될수 있다. 발광층 (230)은호스트로서또다른유기 화합물을더포함할수있다.
발광층 (230)은도펀트를더포함할수있고도펀트는예컨대 인광도펀트일수있다. 일 예로，전술한유기 화합물은전자보조층 (140)에 포함될수있다. 전자 보조층 (140)은전술한유기 화합물을단독으로포함할수도있고전술한유기 화합물중적어도두종류를혼합하여포함할수도있고전술한유기 화합물과 다른유기 화합물을혼합하여포함할수도있다.
도 2에서유기층 (105)으로서추가로애노드 (110)와발광층 (230)사이에 위치하는적어도 1층의 정공보조층 (도시하지 않음)을더 포함할수있다.
상술한유기 발광소자는유기 발광표시 장치에 적용될수있다.
【발명의실시를위한형태】
이하실시예를통하여 상술한구현예를보다상세하게 설명한다. 다만 하기의실시예는단지 설명의목적을위한것이며 권리범위를제한하는것은 아니다.
합성예 1:중간체 1-1의합성
Figure imgf000043_0001
2019/132374 1»(：1/10公018/016133
43
Figure imgf000044_0001
구입한 l-bromo-4-chloro-2-fluorobenzene(60 g， 289 mmol)을 tetrahydrofiiran(THF) 0.5L에녹인 후，여기에 tokyo chemical industry에서 구입한 2,3-dimethoxyphenylboronic acid(57.8 g, 317 mmol)와 tetrakis(triphenylphosphine)palladium(3.34 g， 2.89 mmol)을넣고교반시켰다. 그리고물에포화된 potassuim carbonate(99.7 g， 722 mmol)을넣고 21시간동안 가열하여 환류시켰다.반응완료후반응액에 물을넣고 dichloromethane(DCM)로 주줄한다음 magnesium sulfate anhydrous로수분을제거한후,필터하고감압 농죽하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-1(67.5 g, 88 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C14H12C1F02: 266.0510, found: 266.
Elemental Analysis: C, 63 %; H, 5 %
합성예 2:중간체 1-2의합성
Figure imgf000044_0002
질소환경에서중간체 1-1(67.5 g, 253 mmol)을 boron tribromide solution 1.0M 0.8L에 녹인후， 5시간동안교반하였다.반응완료후반응액을 0 °C로온도를 낮춘후,포화된 sodium thiosulfate수용액 0.8L을 30분간천천히 적가하였다.이후， 물을넣고 dichloromethane(DCM)로주줄한다음 magnesium sulfate anhydrous로 수분을제거한후，필터하고감압농축하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-2(60.0 g, 99 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H18C1F02: 238.0197, found: 238.
Elemental Analysis: C， 60 %; H, 3 %
합성예 3:중간체 1-3의 합성 2019/132374 1»(：1/10公018/016133
44
Figure imgf000045_0001
질소환경에서 중간체 1-2(60.0 g, 253 mmol)를 N-methyl-2-pyrrolidone(NMP) 0.3 L에녹인후,여기에 potassuim carbonate(70.0 g, 506 mmol)을넣고 14시간동안 가열하여환류시켰다.반응완료후용매를증류하여 제거한후반응액에 물을 넣고 dichlorometlmne(DCM)로주줄한다음 magnesium sulfate anhydrous로수분을 제거한후,필터하고감압농축하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-3(40.4 g, 73 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H7C102: 218.0135, found: 218.
Elemental Analysis: C, 66 %; H, 3 %
합성예 4:중간체 1-4의 합성
Figure imgf000045_0002
질소환경에서 중간체 1-3(35生 160 11111101)을 (1 11101011161;1 1½(1) ^1) 0.31세 녹인후, 0 °0로온도를낮췄다.여기에선 0 0파6仕1¥681山［'011 011117 (1€：(54.2 192 mmol)을넣고교반시켰다. 14시간후반응액을 0 °C로온도를낮춘후물을 30분간 천천히 넣고 dichloromethane(DCM)로주줄한다음 magnesium sulfate anhydrous로 수분을제거한후，필터하고감압농축하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-4(55.0 & 98 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C13H6C1F304S: 349.9627, found: 350.
Elemental Analysis: C, 45 %; H， 2 %
합성예 5:중간체 1-5의합성 2019/132374 1»(：1/10公018/016133
45
Figure imgf000046_0001
합성예 1과동일한방법으로중간체 1-4(50 g, 143 mmol)와 tokyo chemical indus仕 y에서 구입한 dibenzofUran-4-ylboronic acid(57.8 g， 157 mmol)을사용하여 중간체 1-5(46.9 g， 89 %)를얻었다.
HRMS (70 eV， EI+): m/z calcd for C24H13C102: 368.0604, found: 368.
Elemental Analysis: C, 78 %; H， 4 %
합성예 6:중간체 1-6의합성
Figure imgf000046_0002
질소환경에서 중간체 I-5(55g， 149 mmol)를 dimethylfomiamide(DMF) 0.5L에 녹인후，여기에 bis(pinacolato)diboron (45.4g, 179mmol)와 (1，1’_
bis(diphenylphosphine)ferrocene)dichloropalladium(II)(1.22g, 1.49mmol)그리고 potassium acetate(43.9g，447mmol)을넣고 150 °C에서 15시간동안가열하여 환류시켰다.반응 완료후반응액에물을넣고혼합물을필터한후,진공오븐에서 건조하였다.
이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-6(48.0 g, 70 %)을얻었다.
Figure imgf000046_0003
460.1846, found : 460.
Elemental Analysis: C, 78 %; H, 5 %
합성예 7:화합물 1의 합성 2019/132374 1»(：1/10公018/016133
46
Figure imgf000047_0001
합성예 1과동일한방법으로중간체 1-6(10 g, 21.7 mmol)과 tokyo chemical industry에서구입한 2-chloro-4,6-diphenyl_l，3,5-triazine(5.81 g, 21.7 mmol)을사용하여 화합물 1(11.7 g， 95 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C39H23N302: 565.1790, found: 565.
Elemental Analysis: C, 83 %; H, 4 %
합성예 8:화합물 2의합성
Figure imgf000047_0002
2
합성예 1과동일한방법으로중간체 1-6(10 g， 21.7 mmol)과 richest group(http:"www.richest-grcmp.com/)에서 구입한 2-(biphenyl-4-yl)-4-chloro-6-phenyl- l，3,5-triazine(7.46 g，21.7 mmol)을사용하여 화합물 2(13.0 g， 93 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H， 4 %
합성예 9:화합물 3의합성 2019/132374 1»(：1/10公018/016133
47
Figure imgf000048_0001
합성예 1과동일한방법으로중간체 1-6(10 g, 21.7 mmol)과 richest group에서 구입한 2-(biphenyl-3-yl)-4-chloro-6-phenyl-l 3：5-triazine(7.46 g, 21.7 mmol)을사용하여 화합물 3(12.8 & 92 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H 4 %
합성예 10:화합물 9의합성
Figure imgf000048_0002
합성예 1과동일한방법으로중간체 1-6(10 g, 21.7 mmol)과 richest group에서 구입한 4-(biphenyl-4-yl)-2-chloro-6-phenylpyrimidine(7.44 g, 21.7
Figure imgf000048_0003
사용하여 화합물 9(13.6 g, 98 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C46H28N202: 640.2151, found: 640.
Elemental Analysis: C5 86 %; H, 4 %
합성예 11:중간체 1-7의합성 2019/132374 1»(：1/10公018/016133
48
Figure imgf000049_0001
1 -7 합성예 1과동일한방법으로 tokyo chemical industry에서구입한 l-bromo-4- chloro-2-fluorobenzene(l 00 g, 478 mmol)와 2,6-dimethoxyphenylboronic acid (95.6 g, 525 mmol)을사용하여중간체 1-7(108 g, 85 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C14H12C1F02: 266.0510, found: 266.
Elemental Analysis: C, 63 %; H, 5 %
합성예 12:중간체 1-8의합성
Figure imgf000049_0002
1 - 7 1 -8
질소환경에서중간체 1-7(108g, 406 mmol)와 pyridine hydrochloride(469 g, 4061mmol)을넣고 180°C에서 12시간동안가열하여 환류시켰다.반응완료후 반응액에 물을넣고 ethylacetate(EA)로주줄한다음 magnesium sulfate anhydrous로 수분을제거한후，필터하고감압농축하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-8(70.6 g, 73 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H8C1F02: 238.0197, found: 238.
Elemental Analysis: C, 60 %; H, 3 %
합성예 13:중간체 1-9의합성 2019/132374 1»(：1/10公018/016133
49
Figure imgf000050_0001
1 - 8 1 -9
합성예 3과동일한방법으로중간체 1-8(70.6 & 296 _01)을사용하여 중간체
1-9(56.0 & 87 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H7C102: 218.0135, found: 218.
Elemental Analysis: C, 66 %; H, 3 %
합성예 14:중간체 1-10의합성
Figure imgf000050_0002
합성예 4와동일한방법으로중간체 1-9(56 g， 256 mmol)을사용하여 중간체 I- 10(89.1 g, 99 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C13H6C1F304S: 349.9627, found: 350.
Elemental Analysis: C, 45 %; H, 2 %
합성예 15:중간체 1-11의합성
Figure imgf000050_0003
2-chloro-6-methoxyphenylboronic acid(l 16g， 629mmol)을사용하여 중간체 1-1 l(120g, 89%)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C13H10C1FO: 236.0404, found: 236.
Elemental Analysis: C, 66 %; H, 4 %
합성예 16:중간체 1-12의합성
Figure imgf000051_0001
1 - 11 1 - 12
합성예 12와동일한방법으로중간체 1-11(115 g, 486 mmol)을사용하여 중간체 1-12(87.6 g, 81 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H8C1FO: 222.0248, found: 222.
Elemental Analysis: C, 65 %; H, 4 %
합성예 17:중간체 1-13의합성
Figure imgf000051_0002
1 - 12 1 - 13
합성예 3과동일한방법으로중간체 1-12(1 10 g, 494 mmol)를사용하여 중간체 1-13(85.1 g, 85 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H7C10: 202.0185, found: 202.
Elemental Analysis: C, 71 %; H, 3 %
합성예 18:중간체 1-14의합성 2019/132374 1»(：1/10公018/016133
51
Figure imgf000052_0001
14
합성예 6과동일한 방법으로 중간체 1-13(81 ¾ 400 _01)을사용하여 중간체
1-14(84.7 & 72 %)를 얻었다.
HRMS (70 eV, EI+): m/z calcd for C18H9B03: 294.1427, found: 294.
Elemental Analysis: C， 74 %; H， 7 %
합성예 19:중간체 1-15의합성
Figure imgf000052_0002
15
합성예 1과 동일한 방법으로 중간체 1-10(50¾ 14311111101)과 중간체 1-14(46.1生
157 11111101)를사용하여 중간체 1-15(42.7& 81%)를 얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H13C102: 368.0604, found: 368.
Elemental Analysis: C, 78 %; H， 4 %
합성예 20:중간체 1-16의합성
Figure imgf000052_0003
합성예 6과 동일한 방법으로 중간체 1-15(40 & 108 11111101)를 사용하여 중간체 1-16(37.3 & 75 %)을 얻었다.
Figure imgf000052_0004
0301525604: 460.1846,及 )1111(1: 460. 2019/132374 1»(：1/10公018/016133
52
Elemental Analysis: C， 78 %; H, 5 %
합성예 21:화합물 30의합성
Figure imgf000053_0001
30
16
합성예 1과동일한방법으로중간체 1-16(10 g, 21.7 mmol)과 richest group에서 구입한 2-(biphenyl-4-yl)-4-chloro-6-phenyl-l,3,5-triazine(7.46 g, 21.7 mmol)을사용하여 화합물 30(13.2 g, 95 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H, 4 %
합성예 22:중간체 1-17의합성
Figure imgf000053_0002
합성예 1과동일한방법으로중간체 1-4(50 g, 143 mmol)와 tokyo chemical industry에서구입한 dibenzothiophen-4-ylboronic acid (35.9 g, 157 mmol)을사용하여 중간체 1-17(48.4 g, 88 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H13C10S: 384.0376, found: 384.
Elemental Analysis: C, 75 %; H, 3 %
합성예 23:중간체 1-18의 합성 2019/132374 1»(：1/10公018/016133
53
Figure imgf000054_0001
합성예 6과동일한방법으로중간체 1-17(47 122 _01)을사용하여 중간체
1-18(40.1 & 69 %)을얻었다.
Figure imgf000054_0002
합성예 1과동일한방법으로중간체 1-18(10 g, 21.0 mmol)과 richest group에서 구입한 2-(biphenyl-4-yl)-4-chloro-6-phenyl-l?3?5-triazine(7.22 g, 21.0 mmol)을사용하여 화합물 46(12.8 & 93 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H27N30S: 657.1875, found: 657.
Elemental Analysis: C, 82 %; H, 4 %
합성예 25:중간체 1-19의합성
Figure imgf000054_0003
19
합성예 1과동일한방법으로 tokyo chemical industry에서 구입한 l-brotno-4 - chloro-2-fluorobenzene( 100g, 482mmol)와 4-chloro-2-me仕 loxyphenylboronic acid(98.8g, 530mmol)을사용하여중간체 I-19(122g, 93%)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C13H9C12FO: 270.0014, found: 270.
Elemental Analysis: C, 58 %; H, 3 %
합성예 26:중간체 1-20의합성
Figure imgf000055_0001
1 - 19 卜 20
합성예 12와동일한방법으로중간체 1-19(120& 443_01)를사용하여 중간체-20(88.8 78 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H8C1FO: 255.9858, found: 256.
Elemental Analysis: C, 56 %; H, 3 %
합성예 27:중간체 1-21의합성
Figure imgf000055_0002
- 20 1 - 21
합성예 3과동일한방법으로중간체 1-20(87 g, 338 mmol)을사용하여 중간체-21(73.0 g, 91 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H6C120: 235.9796, found: 236.
Elemental Analysis: C, 61 %; H, 3 %
합성예 28:중간체 1-22의합성 2019/132374 1»(：1/10公018/016133
55
Figure imgf000056_0001
합성예 6과동일한방법으로중간체 1-21(71 & 299 11111101)를사용하여 중간체
1-22(64.2 ^ 51 %)#얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H30B2O5: 420.2279, found: 420.
Elemental Analysis: C, 69 %; H, 7 %
합성예 29:중간체 1-23의합성
Figure imgf000056_0002
1 - 22 卜 23
합성예 1과동일한방법으로중간체 1-22(62 g, 148 mmol)와 tokyo chemical industry에서 구입한 4-bromodibenzofiiran(32.8 g, 133 mmol)을사용하여 중간체 I- 23(27.6 g, 45 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C30H25BO4: 460.1846, found: 460.
Elemental Analysis: C, 78 %; H, 5 %
합성예 30:화합물 81의합성
Figure imgf000056_0003
합성예 1과동일한방법으로중간체 1-23(10 g, 21.7 mmol)과 richest group에서 구입한 2-(biphenyl-4-yl)-4-chloro-6-phenyl-l,3?5-triazine(7.46 g, 21.7 mmol)을사용하여 2019/132374 1»(：1/10公018/016133
56 화합물 81(13.9 g， 96 %)을얻었다.
HRMS (70 eV， EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H, 4 %
합성예 31:중간체 1-24의 합성
Figure imgf000057_0001
卜 14
합성예 1과동일한방법으로중간체 1-4(50 g, 143 mmol)와중간체 1-14(46.3 g,
157 mmol)를사용하여 중간체 1-24(42.2 g, 80 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H13C102: 368.0604, found: 368.
Elemental Analysis: C, 78 %; H, 4 %
합성예 32:화합물 121의합성
Figure imgf000057_0002
tech(htp :" www.phtech.co.kr/)에서구입한 2,4-(먀1 611:/1-6-(3-(4,4,5,5_1611¾1 及1>4-1,3,2- 0 3¾>0101311-2- 1)|)11611 1)-1,3,5- 3 116(11.8은， 21.711111101)을사용하여 화합물 121(13.2은， 95 %）을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H, 4 %
합성예 33:화합물 Host 1의 합성 2019/132374 1»(：1/10公018/016133
57
Figure imgf000058_0001
Host l
일본공개특허 제 2017-107992호의 합성법을참고하여 화합물 Host l을 합성하였다.
HRMS (70 eV， EI+): m/z calcd for C33H21N30: 475.1685, found: 475.
Elemental Analysis: C, 83 %; H, 4 %
합성예 34:화합물 Host 2의합성
Figure imgf000058_0002
Host 2
일본공개특허 제 2017-107992호의 합성법을참고하여 화합물 Host 2를 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C33H21N30: 475.1685, found: 475.
Elemental Analysis: C, 83 %; H， 4 %
합성예 35:화합물 Host 3의합성
Figure imgf000058_0003
Host 3
한국등록특허 제 10-1788094호의 합성법을참고하여 화합물 1¾ 3을 2019/132374 1»(：1/10公018/016133
58 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C39H23N302: 565.1790, found: 565.
Elemental Analysis: C, 83 %; H, 4 %
합성예 36:화합물 Host 4의합성
Figure imgf000059_0001
Host 4
한국등록특허 제 10-1730779호의 합성법을참고하여 화합물 Host 4를 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H, 4 %
합성예 37:화합물 Host 5의합성
Figure imgf000059_0002
Host 5
한국등록특허 제 10-1730779호의 합성법을참고하여 화합물 Host 5를 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C45H27N302: 641.2103, found: 641.
Elemental Analysis: C, 84 %; H， 4 %
합성예 38:화합물 Host 6의합성 2019/132374 1»(：1/10公018/016133
59
Figure imgf000060_0001
Host 6
미국등록특허 제 8, 541 , 112호의 합성법을참고하여 화합물 Host 6을 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C54H32N202: 740.2464, found: 740.
Elemental Analysis: C, 88 %; H, 4 %
합성예 39:화합물 E-l의 합성
Figure imgf000060_0002
한국공개특허 제 10-2014-0042630호의 합성법을참고하여 화합물 E-1을 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C47H31N3: 637.2518, found: 637.
Elemental Analysis: C, 89 %; H, 5 %
합성예 40:화합물 E-23의함성
Figure imgf000060_0003
한국공개특허 제 10-2014-0042的 0호의 합성법을참고하여 화합물표-23을 합성하였다. 2019/132374 1»(：1/10公018/016133
60
HRMS (70 eV, EI+): m/z calcd for C36H24N2: 484.1939, found: 484.
Elemental Analysis: C, 89 %; H, 5 %
합성예 41:화합물 E-25의합성
Figure imgf000061_0001
한국공개특허 제 10-2014-0042630호의 합성법을참고하여 화합물 E-25를 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C48H30N2: 634.2409, found: 634.
Elemental Analysis: C, 91 %; H, 5 %
합성예 42:화합물 1：-31의합성
Figure imgf000061_0002
한국공개특허 제 10-2014-0042630호의 합성법을참고하여 화합물표-31을 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C48H32N2: 636.2565, found: 636.
Elemental Analysis: C, 91 %; H, 5 %
합성예 43:화합물 F-l의합성 2019/132374 1»(：1/10公018/016133
61
Figure imgf000062_0001
한국공개특허 제 10-2014-0042630호의 합성법을참고하여 화합물 F-1을 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C30H20N2: 408.1626, found: 408.
Elemental Analysis: C， 88 %; H 5 %
합성예 44:화합물 F-43의합성
Figure imgf000062_0002
한국공개특허 제 2017-0026359호의 합성법을참고하여 화합물 F-43을 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C42H28N2: 560.2252, found: 560.
Elemental Analysis: C, 90 %; H, 5 %
합성메 45:화합물 F-58의합성
Figure imgf000062_0003
한국공개특허 제 2016-0048868호의 합성법을참고하여 화합물 58을 합성하였다. 2019/132374 1»(：1/10公018/016133
62
HRMS (70 eV, EI+): m/z calcd for C48H31N3: 649.2518, found: 649.
Elemental Analysis: C, 89 %; H, 5 %
합성예 46:화합물 F-88의합성
Figure imgf000063_0001
한국공개특허 제 2016-0048868호의 합성법을참고하여 화합물 F-88을 합성하였다.
HRMS (70 eV, EI+): m/z calcd for C48H31N3: 649.2518, found: 649.
Elemental Analysis: C, 89 %; H, 5 %
유기발광소자의 제작
Figure imgf000063_0002
실시예 1
ITO (Indium tin oxide)가 1500A의 두께로박막코팅된유리 기판을증류수 초음파로세척하였다.증류수세척이 끝나면이소프로필알코올,아세톤,메탄올 등의용제로초음파세척을하고건조시킨후플라즈마세정기로이송시킨다음 산소플라즈마를이용하여상기 기판을 10분간세정한후진공증착기로기판을 이송하였다.이렇게준비된 ITO투명 전극을양극으로사용하여 ITO기판상부에 화합물 A를진공증착하여 700A두께의 정공주입층을형성하고상기 정공주입층 상부에 화합물 B를 50A의두께로증착한후，화합물 C를 1020A의두께로 증착하여 정공수송층을형성하였다.정공수송층상부에상기에서 합성예 7에서 얻은 화합물 1을호스트로사용하고도판트로트리스 (2 -페닐피리딘)이리듐 (III) [Ir(ppy)3]를 10wt%로도핑하여 진공증착으로 400 A두께의 발광층을형성하였다.이어서상기 발광증상부에 화합물 D와 Liq를동시에 1:1비율로진공증착하여 300A두께의 전자수송층을형성하고상기 전자수송층상부에 Liq l5A과 A1 1200A을순차적으로 진공증착하여 음극을형성함으로써 유기발광소자를제작하였다. 2019/132374 1»（：1^1{2018/016133
63 상기유기발광소자는 5층의 유기 박막층을가지는구조로되어 있으며， 구체적으로다음과같다.
11X3/화합물쇼(700入)/화합물 50入)/화합물 0(1020 A)/EML［화합물
1 :1바? 3=90%: 10%］(400ᅀ)/화합물 0丄 (300요)凡 (15人)/신(1200入)의 구조로 제작하였다.
화합물쇼: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-1½1닌116
화합물 1,4,5,8,9，11 -1½ 크å 14^)11611 16116-116 1)011紅1'116 (11쇼1'- ''1),
화합물 C:N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)- 911-111«ᅲ611-2 11 1½
화합물］〕: 8-(4-(4,6-di(naphthal 611-2-3^1)- 1 ,3 ,5-triazin-2-yl)phenyl)quinolone 실시예 2
발광층호스트로화합물 1 대신합성예 8에서 얻은화합물 2를사용한것을 제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
실시예 3
발광층호스트로화합물 1대신합성예 9에서 얻은화합물 3을사용한것을 제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
실시예 4
발광층호스트로화합물 1대신합성예 10에서 얻은화합물 9를사용한것을 제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
실시예 5
발광층호스트로화합물 1대신합성예 21에서 얻은화합물 30을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
실시예 6
발광층호스트로화합물 1 대신합성예 24에서 얻은화합물 46을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다. 2019/132374 1»（：1^1{2018/016133
64 실시예 7
발광층호스트로화합물 1 대신합성예 30에서 얻은화합물 81을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
실시예 8
발광층호스트로화합물 1대신합성예 32에서 얻은화합물 121을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 1
발광증호스트로화합물 1대신 4,4’- （9-001¾3：201-9- 1）1 1161131（^¾1））를사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 2
발광층호스트로화합물 1 대신합성예 33에서 얻은화합물 110 1을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 3
발광층호스트로화합물 1대신합성예 34에서 얻은화합물 1¾았 2를사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 4
발광층호스트로화합물 1 대신합성예 35에서 얻은화합물 1¾ 3을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 5
발광층호스트로화합물 1대신합성예 36에서 얻은화합물 110 4를사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 6
발광층호스트로화합물 1 대신합성예 37에서 얻은화합물 1½ 5를사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
비교예 7
발광층호스트로화합물 1 대신합성예 38에서 얻은화합물 戒 6을사용한 것을제외하고는실시예 1과동일한방법으로유기발광소자를제작하였다.
Figure imgf000066_0001
1내지 7에 따른유기발광소자의 구동전압， 발광효율및수명특성을평가하였다.
구체적인측정방법은하기와같고，그결과는표 1과같다.
(1)전압변화에 따른전류밀도의 변화측정
제조된유기발광소자에 대해，전압을
Figure imgf000066_0002
부터 10 까지 상승시키면서 전류- 전압계 ( 11 7 2400)를이용하여 단위소자에흐르는전류값을측정하고,측정된 전류값을면적으로나누어 결과를얻었다.
(2)전압변화에 따른휘도변화측정
제조된유기발광소자에 대해，전압을
Figure imgf000066_0003
부터 10¥까지 상승시키면서 휘도계 ( 0血 3-1000시를이용하여 그때의 휘도를측정하여 결과를얻었다.
(3)발광효율측정
상기 (1)및 (2)로부터 측정된휘도와전류밀도및 전압을이용하여 동일 전류밀도 (10 111쇼/0112)의 전류효율 /시을계산하였다.
(4)수명측정
휘도 (1/1112)를 6000。(1/마2로유지하고전류효율 0넜/쇼)이 97%로감소하는 시간을측정하여 결과를얻었다.
[표 1]
Figure imgf000066_0004
Figure imgf000067_0001
표 1을참고하면，실시예 1내지 8에 따른유기발광소자는비교예 1내지 7에 따른유기발광소자와비교하여구동전압,발광효율및수명특성이 현저하게 개선된 것을확인할수있다.
유기 발광소자의 제작 II
실시예 9
ITO (Indium tin oxide)가 1500 A의두께로박막코팅된유리 기판을증류수 초음파로세척하였다.증류수세척이 끝나면이소프로필알코올,아세톤,메탄올 등의용제로초음파세척을하고건조시킨후플라즈마세정기로이송시킨다음 산소플라즈마를이용하여 상기 기판을 10분간세정한후진공증착기로기판을 이송하였다.이렇게준비된 ITO투명 전극을양극으로사용하여 ITO기판상부에 화합물 A를진공증착하여 700 A두께의 정공주입층을형성하고상기 정공주입층 상부에 화합물묘를 50A의두께로증착한후，화합물 C를 1020A의 두께로 증착하여 정공수송층을형성하였다.정공수송층상부에 상기에서 합성예 7에서 얻은 화합물 1과합성예 42에서 얻은화합물 E-31을동시에 호스트로사용하고도판트로 2019/132374 1»（：1^1{2018/016133
67 트리스（2 -페닐피리딘）이리듐（III）［11切?넜3］를 10^%로도핑하여 진공증착으로 400入 두께의 발광층을형성하였다. 여기서 화합물 1과화합물 31은 3:7중량비로 사용되었다.이어서상기 발광층상부에 화합물 £＞와 를동시에 1 :1비율로진공 증착하여 300ᅀ두께의 전자수송층을형성하고상기 전자수송층상부에 0（¾ 15人과 1200人을순차적으로진공증착하여 음극을형성함으로써 유기발광소자를 제작하였다.
상기유기발광소자는 5층의 유기 박막층을가지는구조로되어 있으며, 구체적으로다음과같다.
0/화합물쇼（700入）/화합물 50入）/화합물 C（1020A）/EML［화합물 1 :화합물 E 31:11切 py）3 =兄兄10%］（400入）/화합물 0:1相（300入）/1^（15入）/쇼1（1200入）의구조로 제작하였다 .（ =중량비）
실시예 10
화합물 1 대신합성예 8에서 얻은화합물 2를사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
실시예 11
화합물 1 대신합성예 9에서 얻은화합물 3을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
실시예 12
화합물 1대신합성예 10에서 얻은화합물 9를사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
실시예 13
화합물 1 대신합성예 21에서 얻은화합물 30을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
실시예 14
화합물 1대신합성예 24에서 얻은화합물 46을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다. 2019/132374 1»（：1^1{2018/016133
68 실시예 15
화합물 1 대신합성예 30에서 얻은화합물 81을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
실시예 16
화합물 1 대신합성예 32에서 얻은화합물 121을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
실시예 17
화합물묘-31대신합성예 39에서 얻은화합물 1사용한것을제외하고는 실시예 10과동일한방법으로유기발광소자를제작하였다.
실시예 18
화합물 £-31대신합성예 40에서 얻은화합물표-23을사용한것을제외하고는 실시예 10과동일한방법으로유기발광소자를제작하였다.
실시예 19
화합물묘-31 대신합성예 41에서 얻은화합물표-25를사용한것을제외하고는 실시예 10과동일한방법으로유기발광소자를제작하였다.
실시예 20
화합물 £-31 대신합성예 43에서 얻은화합물 1^-1을사용한것을제외하고는 실시예 10과동일한방법으로유기발광소자를제작하였다.
실시예 21
화합물 £-31 대신합성예 44에서 얻은화합물 43을사용한것을제외하고는 실시예 10과동일한방법으로유기발광소자를제작하였다.
실시예 22
화합물 £-31대신합성예 45에서 얻은화합물 1^-58을사용한것을제외하고는 실시예 10과동일한방법으로유기발광소자를제작하였다.
실시예 23
화합물 £-31 대신합성예 46에서 얻은화합물 1^-88을사용한것을제외하고는 2019/132374 1»（：1^1{2018/016133
69 실시예 10과동일한방법으로유기발광소자를제작하였다.
비교예 8
발광층호스트로화합물 31을단독으로사용한것을제외하고는실시예 9와 동일한방법으로유기발광소자를제작하였다.
비교예 9
화합물 1 대신합성예 33에서 얻은화합물 ¾） 1을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
비교예 10
화합물 1대신합성예 34에서 얻은화합물 ¾ 2를사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
비교예 11
화합물 1 대신합성예 35에서 얻은화합물 1¾ 3을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
비교예 12
화합물 1대신합성예 36에서 얻은화합물 ¾ 4를사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
비교예 13
화합물 1 대신합성예 37에서 얻은화합물 ¾ 5를사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
비교예 14
화합물 1대신합성예 38에서 얻은화합물 1¾ 6을사용한것을제외하고는 실시예 9와동일한방법으로유기발광소자를제작하였다.
Figure imgf000070_0001
14에 따른유기발광소자의 구동전압， 발광효율및수명특성을평가하였다.
그결과는표 2와같다. 2019/132374 1»(：1/10公018/016133
70
[표 2]
Figure imgf000071_0001
표 2를참고하면，실시예 9내지 23에 따른유기발광소자는비교예 8내지 2019/132374 1»（：1^1{2018/016133
71
14에 따른유기발광소자와비교하여 구동전압,발광효율및수명특성이 현저하게 개선된것을확인할수있다.
이상에서본발명의 바람직한실시예들에 대하여 상세하게설명하였지만본 발명의 권리범위는이에 한정되는것은아니고다음의 청구범위에서 정의하고 있는본발명의 기본개념을이용한당업자의 여러 변형 및 개량형태또한본 발명의 권리범위에 속하는것이다.
【부호의 설명】
100, 200:유기 발광소자
105:유기층
110:애노드
120:캐소드
130, 230:발광층
140:전자보조층

Claims

2019/132374 1»（：1^1{2018/016133 72 【청구의 범위】 【청구항 1】 하기 화학식 1로표현되는유기 화합물:
[화학식 1]
Figure imgf000073_0001
상기 화학식 1에서，
方내지 3는각각독립적으로 ^또는 1이고,
Figure imgf000073_0002
적어도둘은 이고,
사1및 /는각각독립적으로수소,중수소，치환또는비치환된 01내지 030알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 피리디닐기,치환또는비치환된피리미디닐기,치환또는비치환된트리아지닐기， 할로겐，시아노기또는이들의조합이고，
느은단일결합또는치환또는비치환된 06내지 020아릴렌기이고，
X1및 X2는각각독립적으로 0또는 이고,
Figure imgf000073_0003
독립적으로수소，중수소,치환또는비치환된 01 내지 030알킬기，치환또는비치환된 06내지。30아릴기，치환또는비치환된 03 내지€30헤테로고리기，치환또는비치환된실릴기,치환또는비치환된아민기, 할로겐，시아노기또는이들의조합이다.
【청구항 2]
제 1항에서，
하기 화학식 1쇼내지 II)중어느하나로표현되는유기 화합물: 2019/132374 1»（：1/10公018/016133
73
［화학식 1시
Figure imgf000074_0001
상기 화학식 1쇼내지 1도＞에서,
公내지 3는각각독립적으로 X또는이 이고, 2019/132374 1»（：1^1{2018/016133
74
7)내지 3중적어도둘은 이고,
사1및사2는각각독립적으로수소,중수소,치환또는비치환된 01내지 030알킬기，치환또는비치환된 6내지 030아릴기，치환또는비치환된 피리디닐기，치환또는비치환된피리미디닐기，치환또는비치환된트리아지닐기, 할로겐,시아노기또는이들의 조합이고,
은단일결합또는치환또는비치환된 6내지 020아릴렌기이고，
X1및 X2는각각독립적으로 0또는 이고，
II1내지요8및 는각각독립적으로수소，중수소，치환또는비치환된€1 내지 030알킬기,치환또는비치환된 06내지 030아릴기，치환또는비치환된 03 내지 030헤테로고리기，치환또는비치환된실릴기，치환또는비치환된아민기, 할로겐，시아노기또는이들의 조합이다.
【청구항 3】
제 2항에서，
상기 화학식 1쇼로표현되는유기 화합물은하기 화학식 1쇼 내지 1쇼1중 어느하나로표현되는유기 화합물:
［화학식 1쇼리
Figure imgf000075_0001
2019/132374 1»(：1/10公018/016133
75
[화학식 1쇼1>]
Figure imgf000076_0002
[화학식 1쇼（1]
Figure imgf000076_0001
는 1이고,
7} ,내지 7}중적어도둘은 X이고, 2019/132374 1»（：1^1{2018/016133
76 사1및 2는각각독립적으로수소，중수소,치환또는비치환된 (：1 내지 30알킬기,치환또는비치환된 06내지 030아릴기,치환또는비차환된 피리디닐기，치환또는비치환된피리미디닐기，치환또는비치환된트리아지닐기, 할로겐,시아노기또는이들의조합이고,
느은단일 결합또는치환또는비치환된 06내지 020아릴렌기이고，
X1및 는각각독립적으로 0또는 이고，
내지묘8및 는각각독립적으로수소，중수소，치환또는비치환된 01 내지 030알킬기，치환또는비치환된 06내지 030아릴기，치환또는비치환된 3 내지 030헤테로고리기,치환또는비치환된실릴기,치환또는비치환된아민기, 할로겐,시아노기또는이들의조합이다.
【청구항 4】
제 2항에서,
상기 화학식 내로표현되는유기 화합물은하기 화학식
Figure imgf000077_0001
18(1중 어느하나로표현되는유기 화합물:
［화학식 내리
Figure imgf000077_0002
2019/132374 1»（：1/10公018/016133
77
［화학식 1 ］
Figure imgf000078_0001
상기 화학식 1묘 내지 1표（1에서， 2019/132374 1»（：1^1{2018/016133
78 X또는 01ᄆ이고,
Figure imgf000079_0001
이고,
사1및쇼 는각각독립적으로수소，중수소，치환또는비치환된 01내지 030알킬기，치환또는비치환된 06내지 030아릴기，치환또는비치환된 피리디닐기,치환또는비치환된피리미디닐기,치환또는비치환된트리아지닐기， 할로겐，시아노기또는이들의조합이고，
은단일결합또는치환또는비치환된 06내지 020아릴렌기이고,
X1및 X2는각각독립적으로 0또는 이고,
내지모8및 는각각독립적으로수소，중수소，치환또는비치환된 01 내지 030알킬기，치환또는비치환된 06내지 030아릴기，치환또는비치환된 03 내지 030헤테로고리기,치환또는비치환된실릴기，치환또는비치환된아민기, 할로겐，시아노기또는이들의조합이다.
【청구항 5】
저 11항에서,
느은단일결합,치환또는비치환된페닐렌기，치환또는비치환된
바이페닐텐기또는치환또는비치환된터페닐렌기인유기 화합물.
【청구항 6]
저 15항에서，
느은단일결합,페닐텐기，바이페닐렌기,터페닐렌기，시아노기 치환된 페닐렌기,시아노기 치환된바이페닐렌기 또는시아노기 치환된터페닐렌기인유기 화합물.
【청구항 7]
제 1항에서,
1및 2는각각독립적으로치환또는비치환된페닐기,치환또는 비치환된바이페닐기，치환또는비치환된터페닐기，치환또는비치환된나프틸기， 치환또는비치환된트리페닐레닐기，치환또는비치환된피리디닐기,치환또는 2019/132374 1»（：1^1{2018/016133
79 비치환된피리미디닐기또는치환또는비치환된트리아지닐기이고，
여기서 치환은적어도하나의수소가중수소，（그1 내지 020알킬기, 06내지 020아릴기,피리디닐기，피리미디닐기,트리아지닐기,할로겐，시아노기또는이들의 조합으로치환된것인유기 화합물.
【청구항 8]
제 1항에서,
X1및 X2는각각 0인유기 화합물.
【청구항 9]
제 1항에서，
하기 그룹 1에 나열된화합물중하나인유기 화합물.
[그룹 1]
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
85
Figure imgf000087_0001
2019/132374 1»（：1^1{2018/016133
87
Figure imgf000088_0001
【청구항 10】
제 1항에 따른제 1유기 화합물,그리고
하기 화학식 2로표현되는카바졸모이어티를포함하는제 2유기 화합물 을포함하는조성물:
[화학식 2]
Figure imgf000088_0002
상기 화학식 2에서,
은단일결합，치환또는비치환된 06내지 030아릴렌기또는 2가의 치환또는비치환된 02내지 030헤테로고리기이고,
은치환또는비치환된 06내지 030아릴기 또는치환또는비치환된 01 내지 30헤테로고리기이고,
Figure imgf000088_0003
독립적으로수소，중수소，치환또는비치환된 01내지 020알킬기,치환또는비치환된 06내지 030아릴기 또는치환또는비치환된 C2내지 030헤테로고리기이고,
묘22내지모25는각각독립적으로존재하거나 II22내지 5중인접한기끼리 연결되어 고리를형성한다.
【청구항 11】
제 10항에서,
상기 제 2유기 화합물은하기 화학식 2쇼로표현되거나하기 화학식 2 1과 2019/132374 1»（：1^1{2018/016133
88
2요-2의조합으로표현되는조성물:
［화학식 2시 ［화학식 26-1］ ［화학식 2묘_2］
Figure imgf000089_0001
상기 화학식 2人화학식 28-1또는화학식 2요-2에서，
V내지 은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기 , 2가의 치환또는비치환된 02내지 030헤테로고리기또는이들의 조합이고，
V내지 은각각독립적으로치환또는비치환된 06내지 030아릴기, 치환또는비치환된 0,2내지 030헤테로고리기 또는이들의 조합이고,
Figure imgf000089_0002
독립적으로수소,중수소，치환또는 비치환된＜그1내지 020알킬기，치환또는비치환된 06내지 030아릴기，치환또는 비치환된 02내지 030헤테로고리기 또는이들의조합이고，
111은 0내지 2의 정수이고，
상기 화학식 2표-1의 인접한두개의 *는상기 화학식 212의 두개의 *와 결합하고,
상기화학식 2 의 나머지 두개의
Figure imgf000089_0003
각각독립적으로수소,중수소，치환또는비치환된 01내지 020알킬기，치환또는 비치환된 06내지 030아릴기,치환또는비치환된€2내지 030헤테로고리기 또는 이들의조합이다.
【청구항 12】
제 11항에서，
상기 화학식 2쇼，화학식 26-1 및화학식 212의 내지쇼3은각각 2019/132374 1»（：1^1{2018/016133
89 독립적으로치환또는비치환된페닐기,치환또는비치환된바이페닐기,치환또는 비치환된터페닐기,치환또는비치환된나프틸기,치환또는비치환된
안트라세닐기，또는치환또는비치환된트리페닐렌기 ,치환또는비치환된
피리디닐기,치환또는비치환된디벤조티오펜일기，치환또는비치환된
디벤조퓨란일기，치환또는비치환된카바졸일기，치환또는비치환된플루오레닐기 또는이들의조합인조성물.
【청구항 13】
제 11항에서，
상기 제 2유기 화합물은하기 화학식 2쇼-1 및 23-&내지 26-6중어느하나로 표현되는조성물:
［화학식 2쇼-1］
Figure imgf000090_0001
2019/132374 1»（：1^1{2018/016133
90
[화학식 26-(1] [화학식 28-6]
Figure imgf000091_0001
상기 화학식 2쇼-1및 26-3내지 28 에서，
V1내지 은각각독립적으로단일결합，치환또는비치환된 06내지〔30 아릴렌기， 2가의 치환또는비치환된 02내지 030헤테로고리기또는이들의 조합이고，
내지 은각각독립적으로치환또는비치환된페닐기,치환또는 비치환된바이페닐기，치환또는비치환된터페닐기，치환또는비치환된나프틸기， 치환또는비치환된안트라세닐기,또는치환또는비치환된트리페닐렌기,치환 또는비치환된피리디닐기,치환또는비치환된디벤조티오펜일기，치환또는 비치환된디벤조퓨란일기,치환또는비치환된카바졸일기,치환또는비치환된 플루오레닐기또는이들의 조합이고,
Figure imgf000091_0002
113(1은각각독립적으로수소,중수소,치환또는 비치환된 (그1내지 020알킬기，치환또는비치환된 C6내지 030아릴기，치환또는 비치환된 02내지 030헤테로고리기 또는이들의 조합이다.
【청구항 14】
서로마주하는애노드와캐소드,그리고
상기 애노드와상기 캐소드사이에 위치하는유기층
을포함하고，
상기유기층은제 1항에 따른유기 화합물또는제 10항에 따른조성물을 포함하는유기 광전자소자.
【청구항 15】 2019/132374 1»（：1^1{2018/016133
91 제 14항에서，
상기유기층은발광층을포함하고，
상기유기화합물또는상기조성물은상기 발광층의 호스트로포함되는 유기 광전자소자.
【청구항 16】
제 14항에 따른유기 광전자소자를포함하는표시 장치.
PCT/KR2018/016133 2017-12-27 2018-12-18 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치 WO2019132374A1 (ko)

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